3-(4-Fluorophenyl)pentanedioic acid

An aqueous solution of sodium hydroxide (3N, 23ML, 69 mmol) was added to a solution of 2-(4-fluorophenyl)-1, 1, 3-trimethoxy carbonyl propane (6.7 g, 21.5 mmol) in methanol (100 ml) at room temperature and the mixture was stirred for 12 hours.. To acetic anhydride (5 ml) was added To a solution of commercial 4- fluorobenzaldehyde (12.4 g) in ethyl acetoacetate (25.3 ml) piperidine (2 ml) was added with stirring at rt. The cloudy solution solidifies within 3 h. The yellow solid was crushed, slurried with ethanol (20 ml), collected by suction filtration, and washed with ethanol. After drying in vacuo 27 g of a faint yellowish solid (the bis- adduct of acetoacetate to the benzaldehyde) was isolated. The powdered solid was added in portions to 40 % NaOH (400 g) with stirring. The resulting yellow slurry was stirred at reflux for 2 h. After cooling in an ice bath the mixture was acidified by portionwise addition of cone. HCI (370 ml) to give a colourless precipitate. The solid was collected by suction filtration and washed with water. After drying in vacuo To a solution of commercial 4-fluorobenzaldehyde (12.4 g) in ethyl acetoacetate (25.3 ml) piperidine (2 ml) was added with stirring at rt. The cloudy solution solidifies within 3 h. The yellow solid was crushed, slurried with ethanol (20 ml), collected by suction filtration, and washed with ethanol. After drying in vacuo 27 g of a faint yellowish solid (the bis-adduct of acetoacetate to the benzaldehyde) was isolated. The powdered solid was added in portions to 40% NaOH (400 g) with stirring. The resulting yellow slurry was stirred at reflux for 2 h. After cooling in an ice bath the mixture was acidified by portionwise addition of conc. HCl (370 ml) to give a colourless precipitate. The solid was collected by suction filtration and washed with water. After drying in vacuo Tetraester 12 (17 g, 45.9 mmol) was dissolved in a 10% KOH solution in ethanol/water (2/1) (170 mL) and heated at reflux for 3 h. The solvent was evaporated under reduced pressure and the residue was acidified with 10% aqueous sulphuric acid and refluxed for 6 h. The reaction mixture was saturated with sodium chloride and extracted with ethyl acetate (3 * 150 mL). The organic extract was dried (Na2SO4) and evaporated to give

Molecular Weight:226.20
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:226.06413699
Monoisotopic Mass:226.06413699
Topological Polar Surface Area:74.6
Heavy Atom Count:16
Complexity:243
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes